CN109971214B - Disperse dark blue dye composition, dye product and application thereof - Google Patents

Disperse dark blue dye composition, dye product and application thereof Download PDF

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CN109971214B
CN109971214B CN201811572441.3A CN201811572441A CN109971214B CN 109971214 B CN109971214 B CN 109971214B CN 201811572441 A CN201811572441 A CN 201811572441A CN 109971214 B CN109971214 B CN 109971214B
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component
disperse dye
dye composition
independently
mass percentage
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CN109971214A (en
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欧其
汪仁良
高怀庆
宋瑜
赵广明
邱雯
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Zhejiang Longsheng Dye Chemical Co ltd
Zhejiang Longsheng Group Co Ltd
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Zhejiang Longsheng Dye Chemical Co ltd
Zhejiang Longsheng Group Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046Mixtures of two or more azo dyes
    • C09B67/0051Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008Preparations of disperse dyes or solvent dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/18Azo dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/82Textiles which contain different kinds of fibres
    • D06P3/8204Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8214Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester and amide groups

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)

Abstract

The invention discloses a disperse dark blue dye composition, a dye product and application thereof. The disperse dye composition comprises a component A and a component B, wherein the ratio of the component A to the component B is (by mass portion) 20-95: 5-80, wherein the component A is at least one selected from compounds shown in the following formula (I), and the component B is at least one selected from compounds shown in the following formula (II). The invention provides a disperse dye product, which contains the disperse dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5: 1. The invention also provides the application of the disperse dye product in printing and dyeing of hydrophobic fiber materials, in particular to the application in printing and dyeing of polyester/spandex and other blended fabrics. When the dye product is applied to printing and dyeing, the lifting force is high, the deep dyeing property is good, and various color fastness is excellent.

Description

Disperse dark blue dye composition, dye product and application thereof
(I) technical field
The invention relates to a disperse dye composition, a dye product and application thereof, in particular to a deep blue disperse dye composition, a dye product prepared from the composition and application of the dye product in dyeing of hydrophobic fiber materials, especially polyester/ammonia blended fabrics.
(II) background of the invention
In recent years, spandex-containing fabrics have become popular internationally, and are increasingly used because they have soft hand, are comfortable to wear, and can exhibit an aesthetic appearance to the human body. Spandex has very high elasticity, and a common product does not use 100% of polyurethane, and is usually made of composite yarn, namely spandex is used as a core, and other fibers are used as a skin layer to make a core-spun yarn elastic fabric, usually a polyester/polyurethane blended fabric. Because the spandex has a special structure and the performance of the spandex is greatly different from that of polyester fiber, disperse dye is easy to dye the spandex, but is easy to desorb when washed with water, so that various fastnesses of products of the type, particularly washing staining fastness, are reduced. AATCC is the American dyer and chemist's Association standard, and is different from the national standard (GB/T series) and the international standard (ISO series) greatly, for example, the color fastness to washing of the same product tested in the series is obviously lower than the color fastness grade in the national standard, and it is necessary to develop a high-fastness disperse dye which can meet the requirements of more than grade 3-4 of the AATCC standard, and the dyeing requirements of polyester/spandex blended fabrics are met.
CN 105419388A discloses a disperse deep blue dye with excellent washing fastness, but the lifting power thereof still leaves room for further improvement.
Disclosure of the invention
The invention aims to provide a disperse dark blue dye composition, a dye product prepared from the composition and application of the dye product in dyeing of hydrophobic fiber materials, particularly polyester/ammonia blended fabrics.
In order to achieve the purpose, the invention adopts the technical scheme that:
on one hand, the invention provides a disperse dye composition, which comprises a component A and a component B, wherein the ratio of the component A to the component B is 20-95 in parts by mass: 5-80, wherein the component A is at least one selected from compounds shown in a formula (I), and the component B is at least one selected from compounds shown in a formula (II);
Figure BDA0001915891730000021
in formula (I):
X1is Cl, Br or cyano;
R1、R2each independently is C1~C4An alkyl group;
R3、R4each independently is-CH2COOK1or-C2H4COOK2In which K is1、K2Each independently is C1~C4An alkyl group; in formula (II):
R5、R6each independently is C1~C4An alkyl group;
m and n are each independently 1 or 2;
ph is phenyl.
In the formulae (I) and (II), said C1~C4The alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.
Preferably, R1、R2Each independently being methyl or ethyl.
Preferably, R3、R4Each independently is-CH2COOK1or-C2H4COOK2In which K is1、K2Each independently being methyl or ethyl.
Preferably, R5、R6Each independently is methyl.
As a further preference, the component a is selected from one of the following formulae or a mixture of two or more thereof:
Figure BDA0001915891730000022
Figure BDA0001915891730000031
it is still further preferred that component A is at least one selected from the group consisting of formulae (I-1) to (I-4).
As a further preference, the component B is selected from one of the following formulae or a mixture of two or more thereof:
Figure BDA0001915891730000041
preferably, the disperse dye composition comprises a component A and a component B, wherein the mass percentage of the component A is 20-95%, and the mass percentage of the component B is 5-80%. Preferably, the disperse dye composition comprises a component A and a component B, wherein the mass percentage of the component A is 30-95%, and the mass percentage of the component B is 5-70%.
Preferably, the disperse dye composition comprises a component A and a component B, wherein the component A accounts for 20-95% by mass, and the component B accounts for 5-80% by mass.
The disperse dye composition can further comprise other dye components. Preferably, the disperse dye composition further comprises a component C, the mass of the component C in the composition is not more than 2 times of the total mass of the component A and the component B, preferably not more than the total mass of the component A and the component B, and the mass of the component C is not 0, and the component C is selected from at least one of the compounds represented by the following formula (III) and/or the following formula (IV):
Figure BDA0001915891730000042
Figure BDA0001915891730000051
in the formula (III):
R7、R8each independently is C1~C4An alkyl group;
R9is benzyl or C1~C4An alkyl group;
R10is C1~C4Alkyl, allyl or-CH2COK3,K3Is C1~C4An alkyl group;
in the formula (IV):
R11、R12each independently is C1~C4An alkyl group;
R13is C1~C4Alkyl or allyl.
In the formulae (III) and (IV), said C1~C4The alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.
Preferably, R7、R8Each independently being methyl or ethyl.
Preferably, R9Is benzyl or ethyl.
Preferably, R10Is methyl, ethyl, n-propyl, allyl or-CH2COK3,K3Preferably methyl.
Preferably, R11、R12Each independently being methyl or ethyl.
Preferably, R13Is methyl, ethyl, n-propyl or allyl.
As a further preference, the component C is selected from one of the following formulae or a mixture of two or more thereof:
Figure BDA0001915891730000052
Figure BDA0001915891730000061
wherein Ph represents a phenyl group;
Figure BDA0001915891730000062
Figure BDA0001915891730000071
it is still further preferred that component C is selected from at least one of the formulae (III-1), (III-2), (IV-1), (IV-2).
The disperse dye composition further preferably comprises a component A, a component B and a component C, wherein the mass percentage of the component A is 20-90%, the mass percentage of the component B is 5-50%, the mass percentage of the component C is 5-65% (preferably 5-50%), and the mass of the component C is not more than 2 times of the total mass of the component A and the component B.
Preferably, the disperse dye composition comprises a component A, a component B and a component C, wherein the mass percentage of the component A is 20-90%, the mass percentage of the component B is 5-50%, and the mass percentage of the component C is 5-65% (preferably 5-50%).
The disperse dye composition particularly preferably comprises a component A and a component B, wherein:
component A is at least one selected from the group consisting of formulae (I-1) to (I-4),
the component B is at least one selected from formulas (II-1) to (II-4),
in the disperse dye composition, the mass percentage of the component A is 20-95%, and the mass percentage of the component B is 5-80%;
or, the disperse dye composition comprises a component A, a component B and a component C, wherein:
the component A is at least one selected from formulas (I-1) to (I-4);
the component B is at least one selected from formulas (II-1) to (II-4);
the component C is at least one selected from the formulas (III-1), (III-2), (IV-1) and (IV-2);
in the disperse dye composition, the mass percentage of the component A is 20-90%, the mass percentage of the component B is 5-50%, the mass percentage of the component C is 5-65%, and the mass of the component C is not more than 2 times of the total mass of the component A and the component B;
or the disperse dye composition consists of a component A, a component B and a component C, wherein:
the component A is at least one selected from formulas (I-1) to (I-4);
the component B is at least one selected from formulas (II-1) to (II-4);
the component C is at least one selected from the formulas (III-1), (III-2), (IV-1) and (IV-2);
in the disperse dye composition, the mass percentage of the component A is 30-95%, the mass percentage of the component B is 5-70%, and the mass percentage of the component C is 5-65%.
In the present invention, the dye compounds of the formulae (I), (II), (III) and (IV) can be conveniently synthesized in a manner known to those skilled in the art, and can be prepared by a method described in patents CN1208057A, CN 102816453A, CN105111104A and EP0439057A or by a similar method, or by a commercially available method.
When the disperse dark blue dye composition is sold as a commodity or directly applied to textile material coloring, an auxiliary agent is usually added for post-treatment.
Therefore, in a second aspect, the invention provides a disperse dye product which can be sold as a commodity or directly applied to textile material coloring, and mainly comprises the disperse dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5: 1. The auxiliary agent is a dispersing agent, other surfactants and the like which are commonly used in the process of compounding disperse dyes, and is preferably selected from one or a mixture of more than two of the following components: naphthalenesulfonic acid-formaldehyde condensates, lignosulfonates, alkylnaphthalenesulfonic acid-formaldehyde condensates (e.g., methylnaphthalenesulfonic acid-formaldehyde condensate (dispersant MF)), naphthalenesulfonic acid-formaldehyde condensate (dispersant NNO), benzylnaphthalenesulfonic acid-formaldehyde condensate (dispersant CNF), sodium lignosulfonates (lignin 85A, lignin 83A), and the like.
Preferably, the disperse dye product consists of the disperse dye composition and an auxiliary agent.
The preparation method of the disperse dye product comprises the following steps:
mixing the dye monomer compounds (crude dyes) which form the disperse dye composition according to a ratio, and then carrying out microparticulation by a grinder such as a sand mill or a grinding machine in the presence of an auxiliary agent and water; alternatively, the dye monomer compound may be subjected to a pulverization treatment using a pulverizer such as a sand mill or a grinder in the presence of an auxiliary agent or water, and then mixed in a certain proportion. The disperse dye product of the present invention is ground into liquid by a sand mill or a grinder, and spray-dried into powder or granules, which is a well-known preparation method for those skilled in the art.
In a third aspect, the invention provides an application of the disperse dye product in printing and dyeing of hydrophobic fiber materials, in particular to an application in printing and dyeing of polyester/spandex and other blended fabrics. The disperse dye product can dye hydrophobic fiber materials in a conventional mode in the industry, such as a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be used for direct printing. Wherein, the common dip-dyeing method comprises the steps of pretreating the hydrophobic fiber material, putting the hydrophobic fiber material into a dye vat for dip-dyeing, washing the hydrophobic fiber material to be neutral by cold water after dyeing, wringing, reducing, washing and drying; the direct printing is to carry out dyeing pretreatment, drying and setting on the fabric, print disperse dye color paste on a printing machine, then carry out steaming, fix the color of the dye on the fabric by using a steaming mode, finally wash and tenter setting.
When the dye product of the present invention is applied to printing and dyeing of textile materials, the technical feature that contributes to the improvement of the dyeing effect is mainly the dye composition contained in the product.
Compared with the prior art, the invention has the beneficial effects that: the disperse deep blue dye product prepared from the disperse deep blue dye composition is used for printing and dyeing of hydrophobic fiber materials, particularly polyester/spandex blended fabrics, has good lifting force, and has excellent fastness such as washing fastness, rubbing fastness, sublimation fastness and the like when being dyed on the polyester/spandex blended fabrics, particularly has outstanding washing fastness.
(IV) detailed description of the preferred embodiments
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1:
the dye can provide deep blue with excellent fastness performance for polyester and blended fabrics thereof after adding 650 g of water into 47 g of a compound shown as a formula (I-1), 17 g of a compound shown as a formula (II-1), 18 g of a compound shown as a formula (III-1), 18 g of a compound shown as a formula (IV-1) and 200 g of a dispersing agent MF, blending, grinding, dispersing and drying to obtain a finished product.
Figure BDA0001915891730000091
Figure BDA0001915891730000101
Example 2:
the dye can provide deep blue with excellent fastness performance for polyester and blended fabrics thereof after adding 650 g of water into 25 g of a compound shown as a formula (I-1), 25 g of a compound shown as a formula (I-2), 10 g of a compound shown as a formula (II-1), 24 g of a compound shown as a formula (III-1), 16 g of a compound shown as a formula (IV-1) and 200 g of a dispersing agent MF and mixing, grinding, dispersing and drying to obtain a finished product.
Figure BDA0001915891730000102
Figure BDA0001915891730000111
Examples 3 to 50:
according to the method described in the embodiment 1 or 2, except that the structures and the weights of the components A-C in the table 1 are adopted, 250 g of the auxiliary agent (200 g of the dispersing agent MF and 50 g of the sodium lignosulfonate) is added, 800 g of water is added to be mixed to prepare slurry, and the slurry is ground, dispersed and dried to prepare the finished product, wherein the dye can provide deep blue with excellent fastness properties for polyester and blended fabrics thereof.
TABLE 1
Figure BDA0001915891730000112
Figure BDA0001915891730000121
Figure BDA0001915891730000131
Example 51:
weighing 2 g of the disperse dye prepared in the embodiments 1-50, treating the terylene/spandex blended fabric by a conventional high-temperature high-pressure dyeing method and heat setting, controlling the dyeing depth (o.w.f) to be 3.0% in the treatment process, adjusting the pH value of a dyeing bath to be 4-5, dyeing at room temperature, raising the temperature to 125 ℃ at 1 ℃/min, keeping the temperature for 45min, reducing, cleaning, washing and drying by a conventional method, and carrying out heat setting at 180 ℃ for 60 seconds to obtain the deep blue dyed fabric. Sublimation, rub and wash fastness were tested according to ISO 105-P01, ISO 105-X12, AATCC 61-2A, respectively:
dyes prepared in examples 1 to 50:
color fastness to sublimation: fading is more than or equal to grade 4, cotton dipping is more than or equal to grade 4-5, and polyester dipping is more than or equal to grade 4-5;
color fastness to rubbing: dry friction is more than or equal to 4-5 grades, and wet friction is more than or equal to 4 grades;
color fastness to washing: the staining of cotton is more than or equal to 4-5 grades, the staining of terylene is more than or equal to 4-5 grades, the staining of acetate fiber is more than or equal to 3-4 grades, and the staining of polyamide is more than or equal to 4 grades.
Comparative example: examples 3 and 23 of patent CN 105419388A were set as comparative examples 1 and 2, respectively.
Example 52:
the dyes of examples 1-50 and comparative examples 1 and 2 were dyed at high temperature and high pressure according to the method of GB/T2397 at dyeing concentrations of 1.5% (C), 3% (2C) and 6% (4C), respectively, and the lifting force performance was evaluated, and the results are shown in Table 2 below:
TABLE 2
Figure BDA0001915891730000132
Figure BDA0001915891730000141
Therefore, when the disperse deep blue dye composition provided by the invention is applied to dyeing, the promotion performance is obviously improved compared with that of the disperse dye in the comparative example.

Claims (10)

1. A disperse dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one compound shown in a formula (I), and the component B is selected from at least one compound shown in a formula (II);
Figure FDA0002600174980000011
in formula (I):
X1is Cl, Br or cyano;
R1、R2each independently is C1~C4An alkyl group;
R3、R4each independently is-CH2COOK1or-C2H4COOK2In which K is1、K2Each independently is C1~C4An alkyl group; in formula (II):
R5、R6each independently is C1~C4An alkyl group;
m and n are each independently 1 or 2;
ph is phenyl;
the component C is at least one selected from compounds shown in the following formula (III) and/or the following formula (IV), based on the component A, the component B and the component C, the mass percentage of the component A is 20-90%, the mass percentage of the component B is 5-50%, the mass percentage of the component C is 5-65%, and the mass of the component C is not more than 2 times of the total mass of the component A and the component B:
Figure FDA0002600174980000012
Figure FDA0002600174980000021
in the formula (III):
R7、R8each independently is C1~C4An alkyl group;
R9is benzyl or C1~C4An alkyl group;
R10is allyl or-CH2COK3,K3Is C1~C4An alkyl group;
in the formula (IV):
R11、R12each independently is C1~C4An alkyl group;
R13is C1~C4Alkyl or allyl.
2. A disperse dye composition according to claim 1, wherein: r1、R2Each independently is methyl or ethyl;
R3、R4each independently is-CH2COOK1or-C2H4COOK2In which K is1、K2Each independently is methyl or ethyl;
R5、R6each independently is methyl; r7、R8Each independently is methyl or ethyl; r9Is benzyl or ethyl; r10Is allyl or-CH2COK3,K3Is methyl; r11、R12Each independently is methyl or ethyl; r13Is methyl, ethyl, n-propyl or allyl.
3. A disperse dye composition according to claim 1, wherein: the disperse dye composition comprises a component A, a component B and a component C, wherein based on the component A, the component B and the component C, the mass percentage of the component A is 20-90%, the mass percentage of the component B is 5-50%, and the mass percentage of the component C is 5-65%.
4. A disperse dye composition according to any one of claims 1 to 3, wherein: the component A is selected from one of the following formulas or a mixture of more than two of the following formulas:
Figure FDA0002600174980000022
Figure FDA0002600174980000031
5. a disperse dye composition according to any one of claims 1 to 3, wherein: the component B is selected from one of the following formulas or a mixture of more than two of the following formulas:
Figure FDA0002600174980000032
Figure FDA0002600174980000041
6. a disperse dye composition according to any one of claims 1 to 3, wherein: the component C is selected from one of the following formulas or a mixture of more than two of the following formulas:
Figure FDA0002600174980000042
Figure FDA0002600174980000051
7. the disperse dye composition according to claim 1,
the disperse dye composition comprises a component A, a component B and a component C, wherein:
the component A is at least one selected from formulas (I-1) to (I-4);
the component B is at least one selected from formulas (II-1) to (II-4);
the component C is at least one selected from the formulas (III-1), (III-2), (IV-1) and (IV-2);
Figure FDA0002600174980000061
Figure FDA0002600174980000071
in the disperse dye composition, based on the component A, the component B and the component C, the mass percentage of the component A is 20-90%, the mass percentage of the component B is 5-50%, the mass percentage of the component C is 5-65%, and the mass of the component C is not more than 2 times of the total mass of the component A and the component B.
8. The disperse dye composition according to claim 1, wherein the disperse dye composition consists of component a, component B and component C, wherein:
the component A is at least one selected from formulas (I-1) to (I-4);
the component B is at least one selected from formulas (II-1) to (II-4);
the component C is at least one selected from the formulas (III-1), (III-2), (IV-1) and (IV-2);
Figure FDA0002600174980000081
Figure FDA0002600174980000091
in the disperse dye composition, based on the component A, the component B and the component C, the mass percentage of the component A is 30-95%, the mass percentage of the component B is 5-70%, and the mass percentage of the component C is 5-65%.
9. A disperse dye product, which comprises the disperse dye composition as claimed in claim 1 and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5: 1.
10. Use of a disperse dye preparation according to claim 9 in printing hydrophobic fibre materials.
CN201811572441.3A 2018-12-21 2018-12-21 Disperse dark blue dye composition, dye product and application thereof Active CN109971214B (en)

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CN105419388B (en) * 2015-10-30 2017-10-20 上海鸿源鑫创材料科技有限公司 A kind of high fastness dispersed deep blue dye composition and dye preparations
EP3178886A1 (en) * 2015-12-10 2017-06-14 DyStar Colours Distribution GmbH High wet fast brilliant blue disperse dye mixtures
CN106497140B (en) * 2016-09-14 2020-10-27 浙江龙盛集团股份有限公司 High-fastness blue-to-black disperse dye composition and dye product
CN106893358B (en) * 2017-01-26 2019-06-18 浙江龙盛化工研究有限公司 It is a kind of blue to black disperse dye composition, dye preparations and application

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